Fifty Shades of DuGrey
by MsEdgely
Summary: Rory Gilmore is going to find out what working for Tristan DuGrey is really like...
1. Chapter 1

_Disclaimer: I do not own the rights to the 'Gilmore Girls' or the 'Fifty Shades' trilogy or the characters involved. I merely thought the title would be a laugh, so I decided to go with it._

_Authors Note: Lemons are a given. This story should be full of lemons, so if you don't like lemons or you're too young to read them, then it's probably best to give this a miss. But I should warn you guys, while I may have derived this storyline from 'Fifty Shades of Grey', in no way do I intend to make this a Dominant/Submissive story._

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Rory could sense the tension in the room as she fumbled over a couple of papers, before nervously clearing her throat. It was just another interview, one more interview where she would make a complete ass out of herself.

And how did she know this? Experience. Experience told her that she sucked when under pressure, which was probably not the best trait to have going straight into an interview. Fortunately her previous work experience had covered all the general bases of the job requirement, so at least she didn't have to worry about feeling stressed _and_ underqualified.

She just needed to relax – find her zen. Otherwise she was going to end up with a bad case of verbal diarrhoea. And considering the usual speed with which she talked, she pretty much sounded like a cartoon chipmunk on speed.

'Sorry about the hold up, I'm sure he'll be with you shortly,' the woman who had led her into the room apologised once again, giving Rory a tight smile as she rummaged through a pile of files on the desk, her burgundy nail polish gleaming back at Rory as she ran her hand over one in particular before pulling it out of the stack.

Her heels clanked loudly against the polished wooden floor as she exited the room, leaving Rory sitting there grasping her resume, feeling the intimidating presence of the large empty chair in front of her.

The door opened once more and Rory was almost certain the secretary had left something behind when she heard a very deep male voice respond to her presence.

'Sorry, I hope I haven't left you waiting too long. I just had some business that needed attending to.'

At the sound of his voice, Rory rose to her feet and turned to face him. Her eyes locked onto his as her mouth dropped open in shock.

Tristan DuGrey stood there, only a few feet away. His hair was shorter than she remembered it being the last time she saw him, but the suit and tie wasn't all that different from the uniform he'd been made to wear while attending Chilton. Rory quickly hid her shock at seeing him again with a smile, as she automatically tucked some loose strands of hair behind her ear.

'Well, this is a little awkward,' she muttered softly, letting out a breathy laugh.

Tristan just stood there staring back at her as the silence lingered between them. His eyes soaked her in, as he gave a brief shake of his head.

'Rory Gilmore. You're the last person I expected to see standing here,' he eventually muttered as he frowned at her in confusion. 'Not that I am complaining, but I never really imagined you being the personal assistant type.'

'Oh, you'd be surprised,' she added quickly, unsure whether she had just been insulted or complimented as she diverted her gaze to the floor.

He motioned for her to take a seat as he made his way around the desk before settling into the large leather chair opposite her.

Rory sat down slowly and started shifting around in her seat, hoping to find some comfort in this strange situation she found herself in. Picking up a pitcher of water that had been sitting on the table, he held it towards one of the glasses on the desk and asked her if she wanted any. Shaking her head politely, she bit her lip and decided to just treat this like any other interview.

So what if the guy who was interviewing her was a blast from the past? She was a grown woman, who had run into plenty of old friends and school mates over the years - she could handle it.

Placing her credentials on the table, Rory decided that clearly this wasn't going to be any ordinary interview and resolved to just go with the flow.

'So you're in charge of this company?' she asked, raising her eyebrows as he poured himself a glass of water, the corners of his lips twitching into a smirk.

'Not the whole company, just this department,' he remarked and after a beat added. 'You would be surprised at the amount a guy can accomplish when he's being holed up in military school.'

'How was that by the way? The last time I saw you, you didn't seem too keen on going,' she asked and found that she was genuinely interested in his answer. She watched on as he rubbed the back of his head before sending her a mischievous smirk.

'It was certainly an experience I'll never forget.'

'So I'm guessing it wasn't all fun and games then,' Rory remarked and couldn't help but smile at the thought. 'It's hard to imagine what you would have been like in a girl-free zone. I mean it must have been pretty tough on you, because if memory serves me correct you were a bit of an extreme dater in high school.'

'Hey, that's not true. I only dated a couple of them,' Tristan said, holding his hands up in his defence.

Rory shook her head in amusement. 'I honestly don't see how that makes it any better, but okay.'

Tristan leaned forward, resting his forearms on the desk as he moved in closer. Rory involuntarily mimicked his actions and then blushed when she realised what she just did, as she pulled back slightly hoping he hadn't noticed.

'What about you?' he asked, his voice taking on a hint of seriousness as his eyes locked on to hers.

Rory couldn't help but fidget. 'What would you like to know?'

'Are you married?'

Taken a little aback by the question, Rory glanced down at her hands and surveyed her jewellery-free fingers. 'No. I mean, there was someone, but it didn't work out.' When she glanced up she caught him studying her expression and quickly blushed. 'I thought you might want to ask me some work related questions?'

'No need,' he quickly stated, as he sat back in his chair. 'You already have the job.'

Rory frowned. 'But you haven't even looked at my credentials yet….'

Tristan merely shrugged at this, as if it were a common inconvenience.

'From what I remember about you Mary, you're more than capable. In fact the minute I saw that it was you in here, I knew I had to hire you.'

'Oh.' She wish she had something better to say than just _oh_, but he caught her off guard. 'Are you sure?'

As soon as the words left her mouth, she felt like slapping her forehead. _Way to go, Rory. The first job offer you get and you question their decision,_ she mentally scolded herself. But a part of her was feeling a little suspicious about his motive – didn't he used to hate her?

He brushed aside her comment as he rose to his feet. 'I'll get Miranda to write up a few legal documents and meanwhile we'll discuss a salary that you feel comfortable with.'

Grabbing the hand rests of her seat, she clutched them as she worked up the nerve to say what was on her mind, and then quickly blurted it out. 'Tristan… Not that I'm ungrateful or anything, but why? I mean, I always thought you sort of hated me after what happened.'

Tristan sent her a meaningful glance, his eyes clouded over with some strange emotion that she couldn't place.

'Mary, I'm not really one to hold a grudge. And besides, I would be an idiot if I let you just walk out of here.'

_Crap_, she just put herself in an awkward position and she knew it too. Clearing her throat as quietly as she could, Rory stared down at her feet as she could feel the tell-tale signs of a blush creeping over her.

'Oh, good.'

'So, are you fine with this? Because if you don't want the position, just tell me now.'

'No. I mean, yes! I want this. I mean, I need this. A job, I mean,' she blurted out and then cringed. 'I'm sounding kind of pathetic now, huh?'

Fortunately for her, Tristan looked more amused than anything else as he held out his hand to her and gave her what she could only describe as a dashing smile. _Boy, was she an idiot, _she mentally kicked herself, wishing that the earth could open up and swallow her whole.

Rubbing her forehead out of mortification, she glanced down at the outstretched hand and hesitated for a second before reaching out and grasping it. He gave her palm a firm squeeze.

'So it's a deal then.'

'I guess so,' Rory agreed, as she smiled back at him. Tristan continued to hold her hand as the seconds ticked by before eventually letting go.

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**I realise not much has happened in the beginning, but I'll make up for it in the next chapter. Please R&R.**


	2. Chapter 2

Disclaimer: I do not own the rights to the 'Gilmore Girls', the 'Fifty Shades' trilogy or the characters involved. I merely thought the title would be a laugh so I decided to go with it.

Authors note: I would like to shout out a big thank you to all the awesome people who reviewed the last chapter: _dvj, luvnliason08, LoVe23, maxfoto, Lyndsey, Skye825, Clg1978, sarah v, erdi99, Guest_. You guys rock!

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Rory stared down at the number written on the sheet before her, trying hard to snap out of the reverie she found herself stuck in as she thought about all the things she could do with this amount of money.

Closing her eyes briefly, she let out a sigh and taped the paper lightly just to make sure it was really there. 'Wow that is a lot of money.'

Opening her eyes which were slightly wider than usual, she looked on at Tristan as he ran the length of his index finger across his lips idly. 'Well the thing is when I hire someone I usually expect them to stay for the long haul. '

Rory picked up the piece of paper and waved it around slightly. 'Well this would do it.'

'So are you happy with that amount?' he asked, his eyes narrowing in on her as he watched her reaction.

'I would seriously be an idiot to turn this down, so yeah. Yeah, I'm pretty happy with it,' she said with a big smile when she realised that she could clear most of her debt and still have money left over. Rory felt like jumping from her chair and doing a happy dance, but the last thing she wanted was for Tristan to think he was hiring a crazy person.

'Anyway, it's a lot of money because I'll be expecting a lot out of you. And this will be including any overtime that I might ask you to do, so as long as you understand that it should be fine.'

'Overtime?'

'Well, you will be on call twenty-four hours of the day, six days a week.'

'Oh,' Rory said in surprise, slowly putting down the piece of paper as the impulse to dance for joy retreated into a distant memory. 'I did not know that.'

'And that includes taking you with me on certain business trips and other occasions, so in reality the wage does cover a broad basis,' Tristan continued on to explain, filling in the blanks as he ran a hand through his short blonde hair.

'What? You mean I have to pay for the trips I go on with you?'

'Uh, no. That will be covered by the company, through the expense account. You won't need to worry about that.'

Rory shifted uncomfortably in her chair once again and hoped that she wasn't going to end up burrowing a hole through the seat with her constant squeamish movements.

Clearly she should have done a_ little _more research on what the job actually required of her. She had just presumed it was going to be another ordinary office job. But attending business trips and other events didn't sound all that bad.

She shrugged her shoulders nonchalantly as her blue eyes brightened with enthusiasm. 'When can I start?'

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Right after she signed a couple of documents, she was led out of the room and directed towards the office manager.

Tristan placed a hand on Rory's back as he introduced the two of them. The guy was dressed smartly and his dark hair was styled in a way that gave him an old Hollywood appeal. His name was Jules and upon seeing her, he instantly gushed over how gorgeous she was and how she was giving off the whole Audrey Hepburn vibe.

After they shook hands, Tristan turned to face her and once again gave her an intense look as if to see how she was coping. 'I need to head off and meet up with some clients. Are you going to be alright if I leave you here with Jules?'

'Sure,' Rory said casually, with a small shrug of her shoulders trying to appear as comfortable as possible. 'I'll just have a look around.'

'Great. Well, as my personal assistant, I'll be giving you a new phone that I can contact you on and basically get you sorted with everything you need by tomorrow evening.'

'Okay, sounds great,' Rory said a little breathlessly, feeling overwhelmed. Tristan must have noticed, because he moved the hand that he had been resting on her back over to her shoulder, and gave her a gentle smile.

'Alright, well, I'll see you tomorrow at five then.'

'Okay,' she replied, acting coy and when she realised this, felt a blush creep over her as the shame settled in.

Jules watched on as Tristan stood there staring at his latest employee for what he thought was longer than necessary before they parted ways.

Rory glanced back at Jules as he stared at her looking lost in thought and she sighed. 'I'm sorry, you probably have so much work to do and here I am, taking you away from it all.'

'Oh, trust me,' he said, snapping to attention as a smile spread across his face. 'It's very rare that I get an opportunity to escape my responsibilities, so you are actually doing me a huge favour.'

Rory smiled back at him as she glanced around the room full of workers behind their desks, typing away on their computers. 'So is this the office I'll be working in?'

Jules motioned towards the office with the flick of his hand. 'Well this is one of them. Every floor has different departments, but this will be the one you'll be in when you need to do some data entry and all that jazz. You realise as a personal assistant you will be an all-arounder, so you'll be in every department at least once.'

'I figured as much,' Rory replied earnestly as they started making their way through the room.

'Well, you look like a capable young woman, so I probably don't need to walk you through every boring detail. But I'll show you around and get you used to the place. So have you ever done this sort of job before?'

Rory shook her head bashfully. 'Honestly, this is my first time as a personal assistant. But I have interned as a journalist for a couple of different newspapers.'

'You interned as a journalist huh? May I ask why you chose to do this line of work instead?'

Funnily enough, Rory felt like she was having more of an interview here then when she was in Tristan's office. She shrugged.

'I just moved into the city and I was finding it hard to get a job in that field, so I decided to expand my horizons.'

'And here you are.'

'Here I am,' Rory replied with a smile.

'Not to scare you or anything, but the last person who took on this job only lasted three days.'

Rory raised both eyebrows at the suggestion. 'You're telling me they quit?'

Jules stared at her for a second before tilting his head back and laughing as if it was the funniest thing in the world. His laughter soon died down and was replaced by a sympathetic smile.

'Oh no, sweetie, Tristan's just very fickle. He knows what he likes.'

'Oh,' Rory said glumly, knowing now that her newly acquired position was probably going to be a temporary one.

He shook his head quickly, as if to reassure her. 'Oh no! Don't take that the wrong way. I only said that because this is the first time I've seen Tristan hire someone on the spot. So it's pretty obvious he likes you.'

'Oh,' Rory said again, feeling a little better with this information. 'Maybe he was just desperate.'

'Trust me when I say this – Tristan's not the kind of guy to get desperate,' he muttered back quietly as if he was letting her in on a secret and for all she knew, he probably was. 'But that's just office gossip talking.'

'Well things really haven't changed that much then,' she said, with a faint smile and saw the confusion shadow his face.

'What do you mean?'

Rory nervously shrugged her shoulders when she realised that might have said something incriminating, so continued to explain. 'Oh, we just used to attend the same high school. It's nothing special.'

'That's interesting,' he said thoughtfully as he nodded his head slowly. Rory could practically see the information sink in.

'Not really,' she replied, pretending to be blasé about it. The last thing she wanted was to feed the office fresh gossip and unwittingly have Tristan find out about it. _Maybe this was the reason why the previous employee only lasted three days, _she thought bemusedly.

Rory decided that when it came to Tristan she was just going to have to shut up and nod her head, just in case she said anything too personal.

'So, I'll show you where your desk will be,' Jules said breaking the silence as she gratefully embraced the change of subject. 'And I just want you to know that if you end up having any trouble, come straight to me. I have been the office manager here for over three years now, so I know pretty much everything there is to know.'

'Okay, but I will be working directly under Tristan right?' she asked slowly.

'Well, you see sweetie, Tristan might be the big boss and you might be working directly under him, but I am the one who keeps this office up and running,' he stated matter-of-factly.

'Noted,' Rory answered back, finding his response oddly amusing. Just like the previous places she interned, she found that the people in positions of authority were always quick to cement their place in the office. And in Jules's case he just let her know that while Tristan was the boss, he was the one who was _really_ in charge.

'Not to sound sexist or anything, but I'm surprised to see so many guys working here,' Rory said, as she couldn't help but notice as they walked through the room that the vast majority of the people sitting behind their desks were men. And the women she did manage to catch a glimpse of appeared to be skirting the age of retirement.

This caused Rory to frown. It just seemed odd that she was the only female there who seemed to be under the age of sixty.

Jules let out a snort. 'Don't worry, no offense taken. It's actually funny you say that, because I was just thinking how out of character it was for Tristan to hire someone like you.'

'What do you mean by that?'

'Well honey, besides the fact that I'm good at what I do, there's a reason why Tristan made me the office manager,' he said and when she gave him a look, he continued on. 'He knows he'll never be tempted to sleep with me and run the risk of either making his life in the office really uncomfortable or potentially run the risk of losing a worker.'

Rory didn't know how she felt about this information. 'Is that office gossip too?'

'Well between you and me, why else would a straight guy only hire guys and old obese women?'

Rory mulled it over and ended up shrugging her shoulders. For all she knew it could be something really innocent, like Tristan trying to break office stereotypes….

'And you think it's strange that he hired me because I don't fit the profile?'

'It's just uncommon in here you see,' he said with the flick of his hand, trying to make it seem unimportant.

'Aren't you worried about making assumptions like that?'

'Ha! If I was worried about that, I would have been fired a long time ago.'

'Fair enough,' she muttered back, deciding not to overthink things.

They stopped short in front of desk that looked pretty much identical to the others she had walked passed.

'So this is where you'll be stationed in here,' Jules explained as she cross-examined the bench space.

'Looks like a nice setup,' Rory remarked as she ran a hand over the keyboard and across the desk.

'I'll have everything organised for you by tomorrow,' he said and then paused before adding. 'And Rory I am being totally honest when I say that I'm happy to have you on board with us here. I'm sure you'll be a great addition to the team.'

'Thanks, I appreciate it,' Rory said, as she gave him a small genuine smile back.

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Rory felt like she was walking on air. The sun seemed brighter, even the god awful coffee tasted better. Things were starting to look up. And when she heard the familiar ring tone of her cell phone, the day perked up even more - especially when she saw who was calling after pulling the phone out of her bag.

Rory flicked the cell open and held it to her ear.

'Hey Peter,' she greeted cheerfully. 'What's up?'

She had originally met Peter through her roommate and after a couple of drinks and some moments of intense debating; they found themselves making out in Rory's bedroom. Not exactly her finest moment, but it had led to what she could only describe as a really sweet first date.

'Hey gorgeous, I was just calling to see if you were still interested in having dinner with me Saturday night?'

A smile spread across her face as she remembered their plans for that night. 'Of course I am,' she said and then added as an afterthought, 'unless you're having second thoughts?'

'Oh no, I was just checking because I didn't hear back from you.'

'I am so sorry about that. I was going to call you tonight,' Rory muttered back apologetically, as she inwardly cringed.

'Alright, well uh, I just wanted to know if you want me to drop around your place and pick you up around eight.'

'Sure, that sounds great.'

Rory was hardly the type to sleep with a guy she just met, especially on the second date. But after being celibate for almost six months, Rory could feel her body screaming at her to do something about it. If she knew in the past that having sex would do this to her, she would have held off for as long as possible because this craving to be touched was seriously starting to get on her nerves.

And Peter…well Peter seemed like a really nice guy, so Rory felt less guilty about buying that set of sexy lingerie for the upcoming date. She didn't see the point of waiting. She always waited and where did it get her?

After Rory got off the phone, she let out a deep sigh and felt the all the tension leave her body. She decided it was time to let her hair loose and enjoy life, so why not start it with a bang? No pun intended.

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** I hope you guys enjoyed the latest chapter! I'm not entirely happy with it, but I usually never am. Anyway, reviews would be much appreciated and would probably even motivate me to write faster. :D**


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